EP0176777A2 — Light curable dental composition

Claim 1

Independent Claim 26 words

A light curable dental composition comprising an ethylenic unsaturated compound and a light polymerization initiator, said light polymerization initiator being selected from the group consisting of:

Claim 2

Dependent Claim 26 words

A light curable dental composition comprising an ethylenic unsaturated compound and a light polymerization initiator, said light polymerization initiator being selected from the group consisting of:

Claim 3

Dependent Claim 228 words

(a) a combination of an organic peroxide and a pyrylium salt compound represented by the following general formula [I] of: wherein R,, R, and R, each represents the same or different atom or group and stands for a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an ethyleyl group, a styryl group, an alkoxy group, a phenyl group, a naphthyl group, an alkylphenyl group, an alkoxyphenyl group, a hydroxyphenyl group, a halophenyl group, a nitrophenyl group, an aminophenyl group, an al- kylaminophenyl group, an alkylaminostyryl group, a nitro group, an amino group or a hydroxyl group, X stands for an oxygen atom or a sulfur atom and Y for an anionic functional group; (b) a polyperoxy ester containing a benzophenone group and represented by the following general formula [II] of: wherein R, and R,' each represents the same or different group and stands for a tertiary alkyl group having 4 to 8 carbon atoms or a tertiary aralkyl group having 9 to 12 carbon atoms and R 2 and R 2 ' each represents the same or different atom or group and stands for a hydrogen atom, a tertiary alkoxy group having 4 to 8 carbon atoms or a tertiary aralkyloxy group having 9 to 12 carbon atoms; and (c) a combination of said polyperoxy ester represented by the general formula [II] and an α-diketone.

Claim 4

Dependent Claim 228 words

(a) a combination of an organic peroxide and a pyrylium salt compound represented by the following general formula [I] of: wherein R,, R, and R, each represents the same or different atom or group and stands for a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an ethyleyl group, a styryl group, an alkoxy group, a phenyl group, a naphthyl group, an alkylphenyl group, an alkoxyphenyl group, a hydroxyphenyl group, a halophenyl group, a nitrophenyl group, an aminophenyl group, an al- kylaminophenyl group, an alkylaminostyryl group, a nitro group, an amino group or a hydroxyl group, X stands for an oxygen atom or a sulfur atom and Y for an anionic functional group; (b) a polyperoxy ester containing a benzophenone group and represented by the following general formula [II] of: wherein R, and R,' each represents the same or different group and stands for a tertiary alkyl group having 4 to 8 carbon atoms or a tertiary aralkyl group having 9 to 12 carbon atoms and R 2 and R 2 ' each represents the same or different atom or group and stands for a hydrogen atom, a tertiary alkoxy group having 4 to 8 carbon atoms or a tertiary aralkyloxy group having 9 to 12 carbon atoms; and (c) a combination of said polyperoxy ester represented by the general formula [II] and an α-diketone.

Claim 5

Dependent Claim 31 words

A composition as claimed in claim 1, wherein 0.0001 to 1 part, by weight, of said pyrylium salt compound is added to 100 parts, by weight, of said ethylenic unsaturated compound.

Claim 6

Dependent Claim 30 words

A composition as claimed in claim 1, wherein 0.001 to 10 parts, by weight, of said organic peroxide is added to 100 parts, by weight, of said ethylenic unsaturated compound.

Claim 7

Dependent Claim 34 words

A composition as claimed in claim 1, wherein 0.01 to 10 parts, by weight, of said polyperoxy ester containing a benzophenone group is added to 100 parts, by weight, of said ethylenic unsaturated compound.

Claim 8

Dependent Claim 29 words

A composition as claimed in claim 1 , wherein 0.01 to 10 parts, by weight, of said a-diketone is added to 100 parts,by weight, of said ethylenic unsaturated compound.

Claim 9

Dependent Claim 18 words

A composition as claimed in claim 1, wherein said ethytenic unsaturated compound is a derivative of methacrylic acid.

Claim 10

Dependent Claim 40 words

A composition as claimed in claim 6, wherein said derivative of methacrylic acid is selected from the group consisting of triethyleneglycol dimethacrylate, hex- amethyleneglycol dimethacrylate, 2.2-bis[4-(3-methacryloxy-2-hydroxy-propoxy)phenyl]propane, di-2-methacryloxyethyl-2,2,4-trimethylhexamethylene dicarbamate, 1,2-bis(3-methacryloxy-2-hydroxypropoxy)ethane, tetramethylolmethane trimethacrylate, 2,2-bis(4-methacryloxyethoxyphenyl)propane, polypropyleneglycol dimethacrylate, methyl methacrylate, 2,2-bis(4-methacryloxy-polyethoxyphenyl)propane and mixtures thereof.

Claim 11

Dependent Claim 47 words

A composition as claimed in claim 1, wherein said organic peroxide is an organic compound having one or more oxygen-oxygen bonds in one molecule, and preferably is selected from the group consisting of lauroyl peroxide, benzoyl peroxide, ditertiarybutyldiperoxy isophthalate, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, 3,3',4,4'-tetra-(tertiarybutylperoxycarbonyl)benzophenone, tertiarybutylperoxybenzoate, tri(tertiarybutylperoxy) trimellitate and mixtures thereof.

Claim 12

Dependent Claim 68 words

A composition as claimed in claim 1, wherein said pyrylium salt compound is selected from the group consisting of 4-(4-butoxyphenyl)-2,6-bis(4-methoxyphenyl)pyrylium fluoroborate, 4-(4-butoxyphenyl)-2,6-bis(4-methoxyphenyl)thiopyrylium fluoroborate, 2,6-bis-(4-methoxyphenyl)-4-phenythiopyrylium fluoroborate, 4-(4-butoxyphenyl)-2,6-diphenylpyrylium fluoroantimonate, 4-(4-dimethylaminophenyl)2,6-diphenyl-thiopyrylium perchlorate, 2,4,6-tri(4-methoxyphenyl)thiopyrylium fluoroborate and mixtures thereof. 10. A composition as claimed in claim 1, wherein said polyperoxy ester containing a benzophenone group is selected from the group consisting of 3,3',4,4'-tetra-(t-butylperoxy-carbonyl)benzophenone. 3,3',4,4'-tetra(t-amylperoxycarbonl)-benzophenone, 3,3',4,4'-tetra-(t-hexylperoxycarbonyl)benzo-phenone, 3,3',4,4'-tetra-(t-octylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(cumylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(p-isopropylcumylperoxycarbonyl)benzophenone, 3,3'-dicarboxy-4,4'-di(t-butylperoxycarbonyl)benzophenone, 3,3'-dicarboxy-4,4'-di(t-hexylperoxycarbonyl)benzophenone and mixtures thereof.

Claim 13

Dependent Claim 43 words

A composition as claimed in claim 1, wherein said α-diketone is an α-diketone having a peak absorption at a wavelength of from 400 nm to 700 nm, and preferably is selected from the group consisting of acenaphthenequinone. 9,10-phenanthrenequinone, camphorquinone, -naphthoquinone and mixtures thereof.

Claim 14

Dependent Claim 39 words

A composition as claimed in claim 1, further comprising fine particles of an inorganic filler, which preferably is selected from the group consisting of apatite, sode-lime glass, quartz, silica, borosilicate glass, alumina, barium oxide, zirconium glass and mixtures thereof.

Claim 15

Dependent Claim 43 words

A composition as claimed in claim 12, wherein said silica has an average particle size of from 1 to 100 millimicrons and is treated to be hydrophobic with a treating agent selected from the group consisting of dimethyldichlorosilane, hexamethyldisilazane, octyltrimethoxysilane and silicone oils.

Claim 16

Dependent Claim 98 words

14 . A composition as claimed in claim 1, further comprising fine particles of an inorganic filler and a high polymer surface active agent, said high polymer surface active agent being a copolymer which is prepared by copolymerizing an unsaturated monomer represented by the following general formula [III] of: wherein R, is a hydrogen atom or a methyl group, R 1 is an alkyl group having 1 to 4 carbon atoms or a phenyl group, and n is an integer of 1 to 15; with an unsaturated ester copolymerizable with said monomer represented by the general formula [III].

Claim 17

Dependent Claim 43 words

A composition as claimed in claim 14, comprising 30 to 80 parts, by weight, of said ethylenic unsaturated compound, 10 to 50 parts, by weight, of said fine particles of said inorganic filler and 0.1 to 20 parts, by weight, of said copolymer.

Claim 18

Dependent Claim 51 words

A composition as claimed in claim 14, wherein said unsaturated monomer represented by the general formula [III] is selected from the group consisting of methoxyethyl acrylate, methoxyethyl methacrylate, methoxydiethyleneglycol acrylate, methoxydiethyleneglycol methacrylate, methoxytetraethyleneglycol acrylate, methoxytetraethyleneglycol methacrylate, isobutoxypolyethyleneglycol acrylate, isobutoxypolyethyleneglycol methacrylate, methoxypolyethyleneglycol acrylate, methoxypolyethyleneglycol methacrylate, phenoxypolyethyleneglycol acrylate, phenoxypolyethyleneglycol methacrylate and mixtures thereof.

Claim 19

Dependent Claim 56 words

A composition as claimed in claim 14, wherein said unsaturated ester copolymerizable with said monomer represented by the general formula [III] is selected from the group consisting of acrylic esters, methacrylic esters and mixtures thereof, preferably from the group consisting of methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate and mixtures thereof.

Claim 20

Dependent Claim 110 words

A composition as claimed in claim 1, wherein said peroxide used in combination with said pyryiium salt compound is a polyperoxy ester containing a benzophenone group and represented by the following general formula [II] of: wherein R, and R,' each represents the same or different group and stands for a tertiary alkyl group having 4 to 8 carbon atoms or a tertiary aralkyl group having 9 to 12 carbon atoms and R, and R,' each represents the same or different atom or group and stands for a hydrogen atom, a tertiany alkoxy group having 4 to 8 carbon atoms or a tertiary aralkyloxy group having 9 to 12 carbon atoms.

Light curable dental composition

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